Copolymers of halo allyl esters of carboxylic acids



Patented Sept. 7, 1948 'UNITED. STATES PATENT oFncr:

COPOLYMERS F HALO ALLYL EST! 01'' OARBOXYLIO ACIDS Albert M. Cliiiord, Stow, om. aloignor to Wingfoot Corporation, Akron, Ohio, a corporation of Delaware This invention relates to plastic masses con- I taining polymerized 2-halo allyl esters and to interpolymers of these esters with other monomeric materials. More particularly, it relates to rubber-like polymers containing a 2-halo allyl ester.

It has been found that the 2-halo allyl esters, especially the 2-chloro allyl esters, of orsanic carboxylic acids may be polymerized to yield useful plastic masses. This is particularly true of interpolymers of the esters with other monomeric substances which may be generally included by the term mono-substituted ethylene Drawing. Application May 16, 1M1.

. Serial No. 393.777

1 Claim. (01. m-oa') 2. that required to secure a latex o! the desired yield and characteristics.

compounds, the vinyl compounds within this .class being especially satisfactory in the formaratio of -80% of the total monomers present but it is preferred to maintain a ratio in which at least 40% of they-halo allyl ester is present.

To illustrate the formation of plastic masses from various of these esters, they were interpolymerized'with butadiene-1,3 in various proportions. The interpolymerization was carried out in an aqueous emulsion containing an emulsifying agent, such as Aquarex'D, Duponol, or other sodium lauryl sulfate type emulsifier, although still other types of emulsifiers may also be employed. A "buffer is added, such as a phosphate-citrate type butler, and an oxidant and a catalyst preferably should also be present. The emulsion follows standard, practice and need not be further described. The temperature of polymerization may range from -80 C. butis usually maintained in the neighborhood of 38-50 C. The time of polymerization will be flvohloroollylacetate To illustrate the preparation of various copolymers, the following typical system is given.

An emulsion was made up containing in water solution the following ingredients;

0% Duponol cubic centimeters 10' Butler solution (Na:I*iPO4 +citric acid) 1 NaBO::.4I-I2O do 0.133

C014 "grams.-- 0. 8

Butadiene and other monomer The 2-chloro allyl ester and the butadiene were added in various proportions and polymerization was conducted with the results noted below:

Other Monomer Ratio p11 g3: Yield,

. -Copolymerswere obtained in each instance,

the properties of these varying from tough to soft. Similar results may be obtained by replacing the butadiene by one of the other monomers mentioned above.

While there have been described above the preferred embodiments of the invention, it will be apparent to those skilled in the art that various modifications and changes may be made therein without departing from the spirit'of the invention or from the scope of the appended claim. 1

I claim:

A copolymer comprising 2-chloroallyl propionate interpolymerized with butadiene-1,3,

Percent The following references file of this patent:

ALBERT M. CLIFFORD.

REFERENCES CITED UNITED s'm'ms PATENTS Number 2,127,660

Name Date Coleman Apr. 28. 1988 are or record 111 the Number 4 Name Date Coleman May 28, 1039 'Brltton June 6, 1939 Brltton June 25, 1940 Britten Sept. 3, 1940 Rothrock Nov. 12, 1940 Pollack Feb. 24, 19,42 Pollack May 5, 1942 D'Ale11o Feb. 9, 1943 Brltton Oct. 5, 1943 

